1. Field of the Invention
The present invention relates to an industrially useful method of producing cis-1-aminoindan-2-ol.
2. Description of the Prior Art
Cis-1-aminoindan-2-ol is important as a medical intermediate. For example, this compound is disclosed as a useful intermediate for producing anti-HIV medicines. See J. Med. Chem., 35, 2525 (1992), J. Med. Chem., 35, 1702 (1992), J. Med. Chem., 35, 1685 (1992), etc. Also, as disclosed in J. Chem. Soc. Chem. Commun., 1992, 1673, it is useful as a material for synthesizing optically-active hydroxyesters. Several methods have been disclosed for producing cis-(.+-.)-1-aminoindan-2-ol. For example, Lutz, et al. [J. Am. Chem. Soc., 73, 1639 (1951)] treated trans-(.+-.)-2-bromoindan-1-ol with concentrated aqueous ammonia to form trans-(.+-.)-1-aminoindan-2-ol, amidated it with benzoyl chloride, and then formed a cis-(.+-.)-2-phenyloxazoline derivative by a ring closure, which was thereafter hydrolyzed to obtain the aimed cis-(.+-.)-1-aminoindan-2-ol. Rittle, et al. (Tetrahedron lett., 1987, 521) introduced cis-(.+-.)-1-aminoindan-2-ol to L-phenylalaninamide, separated the resulting mixture by chromatography, and then used a sodium ethoxide treatment to form optically-active cis-1-(-)-aminoindan-2-ol as follows: ##STR2##
Though the method of Lutz, et al. is relatively effective, it requires multiple steps since the product is made by way of trans-(.+-.)-1-aminoindan-2-ol. Also, it is disadvantageous in that a large quantity of waste water and liquid is yielded as a by-product while the volume efficiency becomes low.
Hassner, et al. [J. Org. Chem., 32, 540 (1967)] heated ethyl-N-(trans-2-iodo-1-indan) carbamate in glyme anhydride to form cis-indano[1,2-d]-2-oxazolidone by a ring closure, which was then hydrolyzed to obtain the aimed cis-(.+-.)-1-aminoindan-2-ol as follows: ##STR3##
However, though the carbamate used as the starting material here can be obtained by an addition reaction of iodoisocyanate to indene, the method of synthesizing iodoisocyanate is difficult and thus has not been considered industrially applicable. Also, it is disadvantageous in that a high temperature is required for forming the oxazolidone and so on.
Didier, et al. [Tetrahedron, 47, 4941 (1991)] reduced 2-oxoindan-1-methyl carboxylate into optically-active cis-(+)-2-hydroxy-1-methyl carboxylate by using baker's yeast. From this optically-active compound, the aimed cis-(+)-1-aminoindan-2-ol and cis-(-)-1-aminoindan-2-ol were obtained by way of multiple synthesis steps as follows: ##STR4##
However, this method is disadvantageous in that an unusual reaction agent is necessary and in that yield is low.
As discussed in the foregoing, there has not been known any satisfactory method for producing cis-1-aminoindan-2-ol. Accordingly, this compound has not easily been made at a low cost in an industrial scale.